A Visitor For Jaina - Pt. 01

As with my previous story, this is 100% fiction, with some parts based loosely on personal fantasies and is not based on actual events. I started this story with the intent of going in a certain direction. While I still ended up in that direction, I became inspired with other possible storylines while I was writing, and I began incorporating pieces of other storylines into this story. I ended up spending a lot of time on the overall story and character development and potential future relationships, but don't worry, the good stuff is still there. I hope you enjoy.

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A quick recap, if you will. My name is Aaron and I'm a software programmer by trade, although my current role with my company is that of an account representative. The money is actually better, but the stress is higher than that of a programmer. As a programmer I just did what I was told. I made software applications work the way our clients wanted them to work. As an account rep, I need to keep the clients happy, but I also need to keep the programmers and others involved in the development of the software happy. Sometimes I must walk a thin line in order to balance the two.

I'm also an unhappily married, closeted crossdresser. I guess should also throw bi-sexual into the mix, now that I have had my first same-sex experience with Shane/Shayla, another crossdresser I met during a recent company conference. Since meeting Shane/Shayla, my wife and I began marriage counseling, but the counseling isn't going well and I'm sure one of us will file for divorce soon. She's still acting like a whore and has been running around with God knows who, and I'm still crossdressing and stepping into the identity of Jaina when I have the chance.

Fast forward to now. It has been about three months since I met Shayla. She was a short, average shaped, but still stunning crossdresser. It was evident that she has been crossdressing regularly for a lot longer than me, given that her makeup was flawless, her voice was feminine, and she carried herself in a way that even would have had me fooled had I not known Shayla was really Shane, a fellow account rep based out of our company's Dallas offices.

I had spent the better part of the last three months travelling between San Diego, where I am based, and the central coast of California, in Santa Barbara. I was working with a client as they upgraded their current system and integrated some of our software packages. It was a lengthy process, and it was expected to take at least another 3 months before the client went live with the new system. While the more frequent than usual trips weren't doing my failing marriage any good, they did give me more of an opportunity to become Jaina.

I hadn't had any further exploits with any other crossdressers since that night I shared with Shayla in Portland. It wasn't that I hadn't tried because God knows I had. As a male, I had never had an urge to suck a cock dry, but as Jaina those curiosities surfaced. I had spent many lonely nights in hotel rooms while travelling for work, dressed as Jaina and imagining what it would be like to go down on another crossdresser as I watched porn. Discovering my wife was cheating on me, coupled with the timing of my trip to Portland, gave me the opportunity to explore those curiosities.

I technically met Shayla in two different ways. The first was through a Doublelist ad I posted about being a crossdresser and wanting to meet with another crossdresser while I was in Portland. The other was through Grindr. Coincidentally, Shayla responded to my Doublelist ad, then checked things out on Grindr and discovered me there. As luck would have it, Shayla was coming to Portland for the same reason and was even going to be staying in the same hotel as me. A few messages later we decided to meet as our male selves in the hotel bar the next night.

Ultimately, we ended up having sex and Jaina and Shayla. We both sucked each other's cocks, and she was all too willing and happy to let me fuck her nice, round ass. We only fucked once during the night, but we spent the night in each other's arms. The next morning it was business as usual. We didn't get a chance to see each other again as Jaina and Shayla before we headed back to our respective homes, but it was a night I would never forget.

A day hadn't passed that I didn't think about Shayla and that night we spent together. I was thinking about her as I sat at my office desk making reservations for my next trip up to Central California. As I printed out the hotel reservation confirmation and my request to use my personal vehicle on the trip, I received an email. A wave of excitement came over me when I saw who it was from...Shane/Shayla.

"Hey, Stranger! Long time, no chat! Gonna be in San Diego in a couple of weeks. Was wondering if you might be available for dinner and drinks? Maybe show us around town?"

Us? Was he bringing someone with him? Before heading to the travel desk to submit my travel paperwork, I hit reply: "Hey! Good to hear from you! What days are you going to be in town? I have been bouncing back and forth between here and Santa Barbara while I oversee the Schuyler project, but I can rearrange dates if I need to." I hit send and headed off to the travel department to turn in my paperwork, feeling a twinge of excitement stirring in my slacks.

The travel department consisted of four cubicles in a large open office area two floors down. It also served as the accounting department, the employee relations department, and the local branch party planning department. Each of the ladies who worked in the travel/accounting/employee relations/party planning department served a different purpose when it came to travel, but all four of them could handle any of the travel related tasks. Jennifer handled everything involved with domestic air travel, Kim handled everything with international travel, including making sure our passports were in order, Samantha handled lodging, and Traci handled incidentals and ensured we had a company credit card for business related expenses.

It was Friday afternoon and things were a little slow when I made my way to their section of the cubicle farm. I found all four of the women were just standing around gossiping when I arrived. "Good afternoon, ladies. I have a personal vehicle use request for my trip to Santa Barbara," I said. Traci perked up immediately at my arrival. Flashing a wide smile that had probably melted the hearts of many men, she beckoned me over. "I'll handle this, girls," she said to the others. "But Kim normally handles my PV requests," I replied. When I said that, Kim giggled as she looked first at Traci, then at me and said, point blank, "But Kim isn't looking for an excuse to flirt with the account rep who insists on using his own car for travel."

I admit, it was rare for people in the company to insist on using their own car for business related travel, but in the long run, it saved the company money. "You know we book a flight up to Santa Barbara and arrange or a rental car for you, Aaron," Traci said as we stepped around to her little piece of the cubicle farm. "I know, I know. We go through this every time, though. It costs the company less money in mileage reimbursement for me to use my car than it would for them to fly me back and forth multiple times a month and rent me a car each time. Besides, the amount they pay in mileage more than covers my actual costs, and I get to pocket the extra. It's a win-win situation."

Traci laughed at the revelation of my little scam. There was absolutely nothing illegal or against any company rules with what I was doing. The government dictated how much had to be paid per mile for travel. It wasn't my fault they paid more per mile than it cost to operate my car, even with California's over-inflated gas prices.

"Okay, smart ass. There you go, one approval for use of a personal vehicle for a trip between San Diego and Santa Barbara. Give me a minute and I'll print you your milage check," she said as she typed a few things into her computer. I had been through this multiple times already, and I knew the distance from our office building in San Diego to our Santa Barbara client's office building was 215.8 miles one-way. At the rate of $0.585 cents per mile, I already knew the check amount was going to be $252.49. Thirty seconds later, with a firm tap of her mouse, Traci told me the check was printing. She just needed to get it signed by the accounts manager. She was gone and back in less than two minutes.

As she returned, check in her outstretched hand, she said, "Hey Aaron, I know this is kind of a personal question to ask, but did something happen between you and your wife? I...ummm...I just noticed you aren't wearing your wedding band anymore." Laughter erupted from Kim's cubicle and Samantha exclaimed, "Oh, please, Trace. You have been eyeing Aaron since the first time you saw him. You didn't 'just' notice he wasn't wearing his ring. You noticed it several months ago." Traci blushed a deep shade of red and shot Samantha a dirty look as she mouthed, "Go fuck yourself, bitch," to her. I felt my own face flush right along with hers.

"Sorry. Forget I asked," she said, returning her attention to me but avoiding eye contact.

"It's alright, Traci. Things are complicated right now. Maybe I can explain some other time."

"No really, I'm sorry. Please, just forget I asked," she whispered, her voice shaking ever so slightly as she returned to her desk and took a seat.

I headed back to my office, my thoughts on what had just happened. Traci was what I would normally think of as "a little cutie". Long, wavy blonde hair, a smile that could light up a room, and a great personality. She was short, standing about 5'3" tall. She was an very attractive young woman in her late 20's or very early 30's, which is why thought of her as "a little cutie". Small and much younger than my 43 years of age.

And not the type I would ever expect to be attracted to the likes of me. For all intents and purposes, I'm a computer nerd and I usually look every bit of the stereotypical computer nerd. Okay, I wear contacts instead of glasses and I don't wear a pocket protector, but to see me and learn what I do for a living, people aren't surprised. I'm neither fat nor skinny. I'm not a gym rat, so I don't look like a jock, which is the type I would have expected Traci to go for, but I jog occasionally, and I ride bicycles regularly, so I manage to keep the extra pounds off. and stay toned. Basically, I'm just an average looking guy.

I got back to my office and all thoughts of Traci and what transpired two floors down immediately left my mind. Shane/Shayla had written back.

"We're going to be in San Diego week after next, from Monday through Thursday. My wife is thinking about accepting a promotion with her job that includes relocating from Dallas to San Diego. I have already inquired, and I will be able to transfer out there while still handling my accounts in the South Region. We want to visit and make sure we like the area before she makes her final decision. So, are you up for it? I know Shayla would love to see Jaina again. ;) Let me know."

Wow. Just wow. My heart started racing and my groin started tingling. I was going to get to see Shayla again, much sooner than I had originally anticipated. Since I had been unsuccessful in meeting anybody since I returned from Portland, I had made up my mind that I was going to make sure Shayla was at the next conference and I fully intended for her and Jaina to spend more time together than the first time. Much more time.

I quickly hit the reply button and told Shane/Shayla that my calendar was clear for the week after next and that I would love to have dinner and drinks and show them around town. I stopped just short of telling them they were welcome to stay at my place. Although my wife was spending more and more time away from home, there were still days and nights she was there and there was still a chance she would be there for a day or two while Shane and his wife were in town. If I needed to, I could always tell her something came up in Santa Barbara with the Schuyler project and that I needed to head up there for a couple of days. It had already happened twice legitimately, and it was likely to happen again, so that story wouldn't have been far-fetched.

The trip to Santa Barbara was uneventful. The parts of the project that had already started were on schedule. Details or the remaining parts of the project were ironed out and we were able to finalize the list of requirements for the remaining parts. I spent my evenings in my hotel room as Jaina. I practiced my makeup...applying, removing, and applying again, trying to achieve a perfect look that would impress Shayla. I spent hours in heels, pacing back and forth in my room, getting used to wearing them for longer periods of time and walking without looking like a clumsy elephant. And I practiced my feminine voice.

I had spent hours watching videos on YouTube that covered all those things and more. Shayla was passable and had no problems going out en femme. I had expressed my insecurities with going out as while dressed, but I wanted to be able to join Shayla for a night on the town as Jaina. At 5'10" tall without heels and between 6'1" and 6'4" depending on which heels I wore and whether they were platform heels or not, it was unlikely I would pass. But 5'10" women weren't unheard of and besides, if I was going to go out in public as Jaina, I was going to do it in an area of the city I knew to be accepting of crossdressers and transgendered women.

My voice was the part that I was most worried about. While I could almost sound like a woman if I was whispering, I sounded like a man trying to speak like a woman when I spoke in a normal tone. My makeup was getting much better, to the point I was almost able to fool myself. I had learned some tips and tricks with contouring and highlighting that "shaped" my face and made it appear more feminine. I had learned the drag technique of gluing my eyebrows down to the point they were virtually invisible, a feat made a bit easier by the fact that I didn't have large brows to begin with. Walking in heels was almost becoming second nature. While I wasn't about to try running in them, I felt confident that I could walk down the street on sometimes uneven pavement and even spend a night dancing in a pair of heels if it came down to that.

I spent my drive back to San Diego on Thursday wondering how things were going to go when Shane and his wife arrived the next Monday. Had he even told her about me and our encounter? He told me he and his wife were both openly bisexual and that they had even shared partners, both men and women, with him dressed as Shayla and with him as his normal male self. Was that his intent? Did he want to share me with her? Did he want me all to himself? All of those were questions that were going to be unanswered until the next Monday.

Friday morning came and I headed into the office. I was thankful that I didn't have any meetings scheduled with any of my other clients. I needed to get some documents typed up and to finalize the Schuyler project and I needed to turn in my receipts. Although the company is very generous when it comes to account reps using company credit cards to pay for business expenses, they still insisted in receipts and reports justifying expenses. Basically, I could take a client out to a 3 Michelin Star restaurant with very few questions asked, but if I spilled wine on my tie while dining at that 3 Michelin Star restaurant, I was going to have to explain why I spent $10 on a new tie at the local Kohl's or Target store.

I got the documents typed up that I needed to get done and I sent them off to the Schuyler representatives for approval. I didn't expect to hear a response until the following Monday or Tuesday at the earliest, and possibly not until later than that. I grabbed my envelope with receipts and headed down to the Travel/Accounting/And Just About Everything Else Department. I walked in and, just like the previous Friday, all four ladies were standing around sharing the latest gossip.

Unlike the previous week where any of the four could have helped me with my personal vehicle request and my mileage reimbursement, Traci was solely responsible for verifying travel receipts and expenses. In all honesty, I hadn't given a second thought to what happened the previous week after I saw the email from Shane.

"Hey Aaron, how was Santa Barbara," she asked as I approached.

"Meh...about the same as usual. A whole lot of the client expecting miracles and yours truly making them think what we were delivering is better than the miracles they are expecting. I'll be glad when this project is finished." I rolled my eyes as I said the last part and Traci must have noticed.

"Well, they're paying us a lot of money. What did you expect? And you know better than me that once the project is finished, it isn't really finished. They are a client, and you are their account rep. It'll be a long time before you're really finished with them. So whatcha got for me this week?"

I handed over my envelope with receipts as she brought up the account information for the card assigned to me. "Nothing out of the ordinary. I bought donuts Tuesday morning, paid for lunch Tuesday and Wednesday, and paid for dinner Wednesday night. Bad Mexican food. I don't recommend the particular restaurant. But then, I really don't recommend Mexican food north of Los Angeles. The farther north you go, the worse it seems to get. I paid for breakfast out of my own pocket, though." Traci raised her eyebrow at me accusingly at my last statement. "Okay, okay, I paid for breakfast out of the leftover money from my mileage reimbursement. Happy?" Traci laughed and I heard chuckles from the other three. It was obvious they were listening to what we were saying.

As Traci finished matching my receipts with the account activity, she turned to me. She kept her eyes down as she lowered her voice. "Listen, Aaron, I... I just wanted to apologize for being so forward with you last week. I just... I saw that you weren't wearing your ring and I thought...."

I interrupted her before she could finish. "Traci, I told you last week that it was okay. Things are just complicated right now. But there's absolutely no need to apologize." She let out a sigh, "Okay. But I'm still sorry." "Then I accept your apology," I replied. After sitting there in awkward silence for a few seconds, I asked, "Is everything in order?" Traci told me it was, and I told her I would see her next week before I turned to leave.

As I was walking away, I remembered Shane and his wife were going to be coming next week. I turned back to the women and told them, "Hey ladies, we have a potential transfer from Dallas coming in next week. Nothing set in stone. It largely depends on whether his wife decides to accept a promotion that is going to require them to relocate here. I might have him come in for a tour of the offices here. If I could trouble one of you to order lunch on Tuesday or Wednesday, I would forever be in your debt."

"I'm sure we can arrange something. We only need about an hour's notice. Just shoot one of us an email to let us know what you want, and we'll take care of the rest," Jennifer replied. After thanking them I headed back to my office to grab my keys and I headed home.

My weekend went by surprisingly quickly. I spent all of Saturday and a good part of Sunday putting together a list of places all over the county that Shane and his wife might be interested in visiting. Most of them were the typical tourist type locations, from Balboa Park and the San Diego Zoo to Oceanside and all points in between. I didn't know what company Shane's wife worked for. For that matter, I didn't even know what she did for a living, but I wanted to show them everything the greater San Diego area had to offer, and I wanted to show them a variety of places they could potentially relocate to.